Key West Bar Crawl Guide

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The southernmost city in the United States, Key West is a stretch of land 3 miles wide by 5 miles long. It was a home to Hemingway, the beginnings of Jimmy Buffett and is still the destination of serious fishermen. Duval Street is home to it all -- legendary bars, live music and ice-cold drinks. Pull up a bar stool and order a pint -- this is the Florida Keys bar crawl experience.

Turtle Kraals Proving that, on a bar crawl, slow and steady wins the race are the Friday night turtle races at Turtle Kraals. The starting line is crossed at 6 p.m., so grab a ticket from the bartender when you order your first round. Place your bets and watch in excitement as a handful of box turtles slowly make their way down a shuffleboard table. At sunset, by which point the turtles should have crossed the finish line, head upstairs to the rooftop bar overlooking beautiful Key West.

Finnegan's Wake
If daiquiris and margaritas aren't your drinks of choice, hit up the $5 pints of Smithwick's offered at Finnegan's Wake on Grinnell Street. Live music provides a lively and festive atmosphere indoors, and outside there's a secluded backyard pub with ample seating. This Irish hideaway has happy hour specials. Check the website for more information.

Hogfish Bar and Grill
Just over the Cow Key Channel Bridge on tiny Stock Island is Hogfish Bar and Grill. Follow Front Street until you stumble upon the historic and iconic watering hole. This noisy haunt is nestled on Safe Harbor Marina, rumored to have been the base of operations for the Bay of Pigs Invasion. Strong drinks go hand in hand with the "Killer" sandwich: hogfish served smothered with Swiss cheese, onions and mushrooms served on fresh Cuban bread. Sure, it's not technically Key West, but Hogfish is the real deal.

Captain Tony's Saloon
Back in Key West proper is the authentic Captain Tony's Saloon. The smoky joint is full of regulars with "back in the day" and "remember when" stories. Before cruise ships lingered in the harbor, Hemingway supposedly drank, reveled and even wrote here. There's a friendly, yet heated, rivalry between Captain Tony's and Sloppy Joe's as to which bar was Hemingway's home away from home. However, Sloppy Joe's can't lay claim to Captain Tony's immortal mention in Jimmy Buffet's "Last Mango in Paradise."

Sloppy Joe's
The other side of the Hemingway debate, Sloppy Joe's is a classic bar still featuring its original early 20th-century wooden ceiling and cracked tile floor. Sloppy Joe's opens in the morning when mimosas and Bloody Marys are served with breakfast, making it the perfect spot to start your Key West pub crawl. Live entertainment is served with lunch and these good vibes continue through the late afternoon and long past sunset.

Durty Harry's A Key West bar with a lively party atmosphere, Durty Harry's features live rock bands almost every night. Listen in the balmy Key West night air at one of the outdoor bars or head upstairs to Rick's, an indoor/outdoor dance club that heats up later in the night. Also located near Durty Harry's and Rick's is the Red Garter, a small strip club where the bouncers remind couples that the "family that strips together sticks together." This is clearly the place to go when you're feeling rowdy.

Green Parrot Bar Green Parrot Bar is the proud home of great drinks and bad art. The walls are adorned with works of local artists -- and not all of them are talented. The bar has been a landmark since 1890, and its open-air set-up is home to friendly bartenders, cold beers and tasty cocktails. While the drinks are delicious, Green Parrot's jukebox is legendary, featuring Chicago, Memphis, Texas and Delta blues.

Best of the Bars Scavenger Hunt
Sign up for Best of the Bars' whirlwind tour of Key West's Duval Street bars combining the fun of drinking with a competitive scavenger hunt. However, you won't be scouring the streets for mundane or weird objects; instead you'll have to solve clues and riddles that will take you to Key West's best bars and hot spots. The tours are normally scheduled every Friday, Saturday and Sunday nights and last about 3 hours. Winners will be announced at the last mystery location and prizes awarded, including dinner gift certificates, bar tabs, free drinks and Key West souvenirs.